1-dodecanamine; dodecylamine -Drug Synthesis Database

【结构式】

【分子编号】40735

【品名】1-dodecanamine; dodecylamine

【CA登记号】124-22-1

【分子式】C₁₂H₂₇N

【分子量】185.35312

【元素组成】C 77.76% H 14.68% N 7.56%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VII)

The alkylation of theobromine (I) with undecenyl mesylate (II) in the presence of NaH in DMSO afforded the 1-undecenyl xanthine (III). Dihydroxylation of the terminal double bond of (III) by means of N-methylmorpholine-N-oxide and a catalytic amount of potassium osmate gave diol (IV), which was further converted to bromo acetate (V) by treatment with a solution of HBr in AcOH. Methanolysis of the bromoester (V) with concomitant cyclization gave rise to epoxide (VI). Finally, epoxide opening upon heating with dodecylamine (VII) furnished the target amino alcohol.

参考文献中间体

合成目标

【1】 Michnick, J.; Underiner, G.E.; Klein, J.P.; Rice, G.C.; Sunkara, P.S. (Cell Therapeutics, Inc.); Second messenger cell signaling inhibitors. CH 686830; EP 0719267; JP 1996508981; US 5470878; WO 9422863 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	16651	theobromine; 3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione	83-67-0	C₇H₈N₄O₂	详情	详情
(II)	50459	10-undecenyl methanesulfonate		C₁₂H₂₄O₃S	详情	详情
(III)	50460	3,7-dimethyl-1-(10-undecenyl)-3,7-dihydro-1H-purine-2,6-dione		C₁₈H₂₈N₄O₂	详情	详情
(IV)	50461	1-(10,11-dihydroxyundecyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione		C₁₈H₃₀N₄O₄	详情	详情
(V)	50462	1-(bromomethyl)-10-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)decyl acetate		C₂₀H₃₁BrN₄O₄	详情	详情
(VI)	50463	3,7-dimethyl-1-[9-(2-oxiranyl)nonyl]-3,7-dihydro-1H-purine-2,6-dione		C₁₈H₂₈N₄O₃	详情	详情
(VII)	40735	1-dodecanamine; dodecylamine	124-22-1	C₁₂H₂₇N	详情	详情

合成路线2

该中间体在本合成路线中的序号：

Bromination of ethyl 4-hydroxybenzoate (I) by means of N-bromosuccinimide and HBF4.Et2O produced ethyl 3-bromo-4-hydroxybenzoate (II), which was further iodinated to (III) employing I2 and K2CO3. Subsequent condensation of (III) with ethylene glycol under Mitsunobu conditions afforded (hydroxyethyl)ether (IV). Palladium-catalyzed coupling of (IV) with 3-chlorophenylboronic acid (V) gave rise to terphenyl derivative (VI). Amide (VII) was then obtained by treatment of ester (VI) with n-dodecylamine in the presence of butyllithium. Finally, alcohol (VII) oxidation using N-methylmorpholine-N-oxide and tetrapropylammonium perruthenate furnished the title carboxylic acid.

参考文献中间体

合成目标

【1】 Butera, J.A.; Caufield, C.E.; Greenfield, A.; Gundersen, E.G.; Lennox, J.R.; Graceffa, R.F.; Mayer, S.C.; Katz, A.H.; McDevitt, R.E.; Havran, L.M. (American Home Products Corp.); 2,3,5-Substd. biphenyls useful in the treatment of insulin resistance and hyperglycemia. WO 9961410 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	40735	1-dodecanamine; dodecylamine	124-22-1	C₁₂H₂₇N	详情	详情
(I)	13492	ethyl p-hydroxybenzoate; ethyl 4-hydroxybenzoate	120-47-8	C₉H₁₀O₃	详情	详情
(II)	39756	ethyl 3-bromo-4-hydroxybenzoate		C₉H₉BrO₃	详情	详情
(III)	39757	ethyl 3-bromo-4-hydroxy-5-iodobenzoate		C₉H₈BrIO₃	详情	详情
(IV)	39758	ethyl 3-bromo-4-(2-hydroxyethoxy)-5-iodobenzoate		C₁₁H₁₂BrIO₄	详情	详情
(V)	39759	3-chlorophenylboronic acid	63503-60-6	C₆H₆BClO₂	详情	详情
(VI)	39760			C₂₃H₂₀Cl₂O₄	详情	详情
(VII)	39761			C₃₃H₄₁Cl₂NO₃	详情	详情

Extended Information